Cheap flights Chicago — Boston (CHI — BOS)

Good to know - Cheap tickets Chicago — Boston

Cheapest flight found $34
Minimal flight time 1h 59m
Flight distance 1366 km
Most popular airline Delta Air Lines

Airfare Chicago – Boston by month

Here you can find out in what months how much a ticket Chicago – Boston costs to buy cheap plane tickets.

Month One-way Round-trip
September 2026
July 2026
June 2026
May 2026
April 2026
March 2026
February 2026
January 2026
December 2025
November 2025
October 2025
September 2025

Remember that the optimal time for booking air tickets is 59 days before the departure date, this is the average time at which air tickets were sold at the lowest prices.

Schedule of direct flights Chicago — Boston

Departure Arrival Flight days Flight Airlines Flight time Airports
00:15 03:39 mon AA665 American Eagle 2h 24m O'Hare International Airport — Logan International Airport Select dates
05:30 08:45 mon, tue, fri, sun WN4825 Southwest Airlines 2h 15m Chicago Midway International Airport — Logan International Airport Select dates
06:00 09:15 sat WN4825 Southwest Airlines 2h 15m Chicago Midway International Airport — Logan International Airport Select dates
06:15 09:30 mon, thu, fri, sat, sun UA2104 United Airlines 2h 15m O'Hare International Airport — Logan International Airport Select dates
06:45 10:03 mon B6312 JetBlue 2h 18m O'Hare International Airport — Logan International Airport Select dates
07:00 10:23 mon, wed, thu, sun AA3710 American Eagle 2h 23m O'Hare International Airport — Logan International Airport Select dates
07:05 10:36 daily DL5641 Delta Air Lines 2h 31m O'Hare International Airport — Logan International Airport Select dates
07:05 10:40 mon, wed, sat, sun DL5633 Delta Air Lines 2h 35m O'Hare International Airport — Logan International Airport Select dates
07:15 10:34 mon, tue, wed, sat, sun UA2067 United Airlines 2h 19m O'Hare International Airport — Logan International Airport Select dates
07:15 10:51 sun AA4458 American Eagle 2h 36m O'Hare International Airport — Logan International Airport Select dates
All routes

Sales of tickets from Chicago to Boston in the last 48 hours

Flights Chicago — Boston

The selection of cheap flights Chicago — Boston

Here you can find and purchase the cheapest flights Chicago — Boston from $34 and Chicago — Boston — Chicago from $20.

The price of the flight Chicago — Boston (United States) — Chicago from $20 (round-trip).

The average price of the flight Chicago — Boston (United States) — Chicago $258 (round-trip).

Low cost flights Chicago — Boston (CHI — BOS)

The distance between Chicago and Boston 849 miles (or 1366 kilometres).

The time difference between Chicago and Boston is 1 h.

Minimal flight time from Chicago to Boston 1h 59m.

LowCostClub always do a comparison of airfares Chicago — Boston with several airlines (include American Eagle, Southwest Airlines, United Airlines). They will always give you all available options so you can find the cheapest flight to Boston. In addition, you can choose the platform where you want to place your orders. There are also special offers for air tickets Chicago — Boston. Last week, for instance, the cheapest round-trip prices stood at $20 while the cheapest one-way price that was available within the last week cost $34

Routes from nearby cities to Boston

A flight from a neighbouring city can help you save money on plane tickets.

The most frequent flight to Boston is from South Bend. The cheapest airfare can be purchased with a flight from Madison from $59. The nearest airports from Chicago with a flight to Boston are in Fort Wayne.

Popular International routes from Chicago

Popular routes from Boston

If you are going to fly from Boston, then study the popular flights. The most popular flights from Boston:

Popular domestic routes from Chicago

FAQ about Chicago — Boston

Yes, they do: AA665, WN4825, UA2104, B6312, AA3710, DL5641, DL5633, UA2067, AA4458, AA4809, AA4760, UA2183, AA1457, UA567, WN3678, WN987, YX9928, UA399, DL5685, AA3359, AA2700, DL5593, AA4404, WN3680, AA4253, AA4385, AA2121, WN1773, AA867, UA1693, DL5859, WN2657, AA4650, DL972, UA1677, UA1983, DL5722, DL5607, AA1033, UA1989, WN4806, , AA4582, DL416, B61012, AA2449, UA2106

Yes, you can fly from Chicago to Boston. Chicago has 8 airports (Merrill C Meigs, DuPage Airport, Chicago Midway International Airport, Chicago NAS, Chicago Executive Airport, Chicago FSS, Chicago Rockford International Airport, O'Hare International Airport) for flights. American Eagle, Southwest Airlines, United Airlines, JetBlue, Delta Air Lines, Republic Airways, Jet Linx Aviation depart from Chicago on mon, tue, wed, thu, fri, sat, sun. There are non-direct flights through Aer Lingus, Aeromexico, Air Canada, Air France, Alaska Airlines, Allegiant Air, Amazon Air, Arajet, Atlas Air, Austrian Airlines, avianca, Breeze Airways, British Airways, Cape Air, Cathay Pacific, Contour Aviation, Copa Airlines, Emirates, Etihad Airways, FedEx, Frontier (Adams the Green Salamander Livery), Iberia, Icelandair, Japan Airlines, Kalitta Charters, KLM, Korean Air, Lufthansa, NetJets, Porter, Porter Airlines Canada, Qatar Airways, SAS, Spirit Airlines, Sun Country Airlines, Swiss, TAP Air Portugal, Turkish Airlines, UPS, Virgin Atlantic.

A direct flight lasts an average of 1h 59m, during which time the aircraft covers a distance of 1366 km.

The price of flights Chicago — Boston starts from $34.

Planes fly Chicago — Boston 7 times a week on the following days: mon, tue, wed, thu, fri, sat, sun

In Chicago — Merrill C Meigs, DuPage Airport, Chicago Midway International Airport, Chicago NAS, Chicago Executive Airport, Chicago FSS, Chicago Rockford International Airport, O'Hare International Airport. In Boston — Pease Air Force Base, Logan International Airport, Boston City Heliport.

The following flights fly between Chicago and Boston: AA665, WN4825, WN4825, UA2104, B6312, AA3710, DL5641, DL5633, UA2067, AA4458, AA4458, AA4458, UA2067, UA2067, UA2067, AA4458, UA2067, UA2067, UA2067, B6312, AA3710, AA4809, AA4760, AA4760, AA4809, UA2183, AA1457, AA1457, AA1457, UA567, WN3678, WN987, AA1457, WN987, YX9928, UA399, UA399, B6312, DL5685, UA399, UA399, UA399, AA3359, AA2700, DL5593, AA4404, AA4404, WN3680, AA4253, AA4385, AA2121, WN1773, AA867, UA1693, UA1693, DL5859, WN2657, WN3680, AA867, AA867, AA4650, DL972, UA1677, DL972, UA1677, UA1983, UA1677, UA1677, UA1677, WN3680, UA1677, DL5722, DL5722, DL5607, AA1033, WN987, UA1989, UA1989, AA1033, WN4806, AA4582, DL416, AA4650, AA4650, B61012, WN1773, B61012, AA4650, AA2449, B61012, WN1773, UA2106

High season is considered to be and the cheapest month is . Enter your preferred airports (or cities) and dates into the search form above to unlock the latest Chicago — Boston flight deals.

The following airlines have direct flights Chicago — Boston: American Eagle, Southwest Airlines, United Airlines, JetBlue, Delta Air Lines, Republic Airways, Jet Linx Aviation.

All the following airlines flights Chicago — Boston: Aer Lingus, Aeromexico, Air Canada, Air France, Alaska Airlines, Allegiant Air, Amazon Air, American Eagle, Arajet, Atlas Air, Austrian Airlines, avianca, Breeze Airways, British Airways, Cape Air, Cathay Pacific, Contour Aviation, Copa Airlines, Delta Air Lines, Emirates, Etihad Airways, FedEx, Frontier (Adams the Green Salamander Livery), Iberia, Icelandair, Japan Airlines, Jet Linx Aviation, JetBlue, Kalitta Charters, KLM, Korean Air, Lufthansa, NetJets, Porter, Porter Airlines Canada, Qatar Airways, Republic Airways, SAS, Southwest Airlines, Spirit Airlines, Sun Country Airlines, Swiss, TAP Air Portugal, Turkish Airlines, United Airlines, UPS, Virgin Atlantic.

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